CA2611266A1 - Utilisation de conjugues avec des lieurs clivables par photodissociation ou par fragmentation a des fins d'analyse par spectrometrie de masse des parties du tissu - Google Patents
Utilisation de conjugues avec des lieurs clivables par photodissociation ou par fragmentation a des fins d'analyse par spectrometrie de masse des parties du tissu Download PDFInfo
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- CA2611266A1 CA2611266A1 CA002611266A CA2611266A CA2611266A1 CA 2611266 A1 CA2611266 A1 CA 2611266A1 CA 002611266 A CA002611266 A CA 002611266A CA 2611266 A CA2611266 A CA 2611266A CA 2611266 A1 CA2611266 A1 CA 2611266A1
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
- G01N33/6851—Methods of protein analysis involving laser desorption ionisation mass spectrometry
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J49/00—Particle spectrometers or separator tubes
- H01J49/004—Combinations of spectrometers, tandem spectrometers, e.g. MS/MS, MSn
- H01J49/0045—Combinations of spectrometers, tandem spectrometers, e.g. MS/MS, MSn characterised by the fragmentation or other specific reaction
- H01J49/0059—Combinations of spectrometers, tandem spectrometers, e.g. MS/MS, MSn characterised by the fragmentation or other specific reaction by a photon beam, photo-dissociation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
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- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Peptides Or Proteins (AREA)
- Electron Tubes For Measurement (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
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| PCT/IB2006/002309 WO2007000669A2 (fr) | 2005-06-07 | 2006-06-07 | Utilisation de conjugues avec des lieurs clivables par photodissociation ou par fragmentation a des fins d'analyse par spectrometrie de masse des parties du tissu |
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| CA002611297A Abandoned CA2611297A1 (fr) | 2005-06-07 | 2006-06-07 | Utilisation de matrices ioniques pour l'analyse par la spectrometrie de desorption-ionisation par impact laser assistee par matrice |
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| JP5072682B2 (ja) * | 2008-03-28 | 2012-11-14 | 富士フイルム株式会社 | 質量分析用デバイス、これを用いる質量分析装置および質量分析方法 |
| JP5092861B2 (ja) * | 2008-04-14 | 2012-12-05 | 株式会社島津製作所 | 混合液体マトリックスを用いたmaldi質量分析法 |
| WO2010141763A1 (fr) * | 2009-06-03 | 2010-12-09 | Wayne State University | Spectrométrie de masse utilisant une technique d'ionisation par pulvérisation laser |
| EP3236264A3 (fr) | 2009-10-13 | 2017-11-08 | Nanostring Technologies, Inc | Détection de protéine par l'intermédiaire de nanorapporteurs |
| WO2011073740A1 (fr) * | 2009-12-15 | 2011-06-23 | Centre National De La Recherche Scientifique (Cnrs) | Matrices pour imagerie par spectrométrie de masse |
| US10787701B2 (en) | 2010-04-05 | 2020-09-29 | Prognosys Biosciences, Inc. | Spatially encoded biological assays |
| CA2794522C (fr) | 2010-04-05 | 2019-11-26 | Prognosys Biosciences, Inc. | Tests biologiques a codage spatial |
| US20190300945A1 (en) | 2010-04-05 | 2019-10-03 | Prognosys Biosciences, Inc. | Spatially Encoded Biological Assays |
| US9523680B2 (en) | 2010-06-30 | 2016-12-20 | Ambergen, Inc. | Global Proteomic screening of random bead arrays using mass spectrometry imaging |
| ES2676183T3 (es) | 2010-07-02 | 2018-07-17 | Ventana Medical Systems, Inc. | Detección de dianas usando marcas de masa y espectrometría de masas |
| GB201106254D0 (en) | 2011-04-13 | 2011-05-25 | Frisen Jonas | Method and product |
| FR2976076B1 (fr) | 2011-05-31 | 2015-02-27 | Imabiotech | Procede de detection et de quantification d'une molecule cible dans un tissu |
| EP2736533B1 (fr) * | 2011-07-29 | 2018-07-04 | Avelas Biosciences, Inc. | Molécules de délivrance sélective et procédés d'utilisation |
| EP2819702A4 (fr) * | 2012-02-29 | 2015-05-20 | Ambrx Inc | Nouveau promédicament contenant des compositions moléculaires et leurs utilisations |
| DK3511423T4 (da) | 2012-10-17 | 2024-07-29 | Spatial Transcriptomics Ab | Fremgangsmåder og produkt til optimering af lokaliseret eller rumlig detektion af genekspression i en vævsprøve |
| EP2767832A1 (fr) | 2013-02-18 | 2014-08-20 | Imabiotech | Conjugués chemolabiles ou photos pour la détection de molécules |
| US9645138B2 (en) | 2013-02-25 | 2017-05-09 | Imabiotech | Method to evaluate the tissue targeting of a molecule of interest |
| WO2014176435A2 (fr) | 2013-04-25 | 2014-10-30 | Bergo Vladislav B | Compositions de microréseaux et leurs procédés d'utilisation |
| US9868979B2 (en) | 2013-06-25 | 2018-01-16 | Prognosys Biosciences, Inc. | Spatially encoded biological assays using a microfluidic device |
| US10041949B2 (en) * | 2013-09-13 | 2018-08-07 | The Board Of Trustees Of The Leland Stanford Junior University | Multiplexed imaging of tissues using mass tags and secondary ion mass spectrometry |
| WO2015128272A2 (fr) * | 2014-02-26 | 2015-09-03 | Ventana Medical Systems, Inc. | Procédé photo-sélectif utilisable dans le domaine de l'analyse d'échantillons biologiques |
| DE102015003440A1 (de) * | 2015-03-16 | 2016-09-22 | Friedrich-Schiller-Universität Jena | Verfahren zur MALDI-MSI Analytik von Objekten, insbesondere biologischen Gewebeproben, und Target zur Analytik sowie dessen Herstellung |
| WO2016162309A1 (fr) | 2015-04-10 | 2016-10-13 | Spatial Transcriptomics Ab | Analyse de plusieurs acides nucléiques spatialement différenciés de spécimens biologiques |
| KR102545430B1 (ko) | 2015-07-17 | 2023-06-19 | 나노스트링 테크놀로지스, 인크. | 절편화된 조직의 사용자-한정된 영역에서의 복수의 단백질의 동시적인 정량화 |
| WO2017015099A1 (fr) * | 2015-07-17 | 2017-01-26 | Nanostring Technologies, Inc. | Quantification simultanée de l'expression génique dans une région définie par l'utilisateur d'un tissu en coupe transversale |
| EP3882357B1 (fr) | 2015-12-04 | 2022-08-10 | 10X Genomics, Inc. | Procédés et compositions pour l'analyse d'acide nucléique |
| WO2017151748A1 (fr) * | 2016-03-01 | 2017-09-08 | Trustees Of Boston University | Libération stimulée par la lumière de chargement à partir d'oligonucléotides |
| GR20160100143A (el) * | 2016-04-11 | 2017-11-30 | Αχιλλεας Αλεξανδρος Βαϊρης | Ελεγχος κατεργασιων συγκολλησης με τριβη |
| EP3336546B1 (fr) * | 2016-12-13 | 2020-07-01 | Miltenyi Biotec B.V. & Co. KG | Marquage de cellules réversible avec des conjugués ayant deux sites de liaison libérable |
| JPWO2018143357A1 (ja) * | 2017-02-01 | 2019-11-21 | 国立大学法人浜松医科大学 | 標的物質と親和性の高い物質をスクリーニングする方法 |
| US11391729B2 (en) | 2017-09-07 | 2022-07-19 | Adeptrix Corp. | Multiplexed bead arrays for proteomics |
| CN112154216B (zh) | 2018-02-12 | 2024-12-27 | 布鲁克空间生物学公司 | 生物分子探针以及检测基因和蛋白表达的方法 |
| CN109917058A (zh) * | 2019-03-14 | 2019-06-21 | 南京农业大学 | 细胞内四种游离脱氧核苷酸的高效液相测定方法 |
| JP7384358B2 (ja) * | 2020-04-27 | 2023-11-21 | 株式会社島津製作所 | 有機化合物の構造解析方法 |
| GB2626908B (en) * | 2020-10-29 | 2025-07-16 | Ambergen Inc | Methods of using photocleavable mass-tags comprising nucleic acid probes for multiplexed mass spectrometric imaging of tissues |
| CN113861074B (zh) * | 2021-09-23 | 2025-01-24 | 中国检验检疫科学研究院 | 一种离子液体maldi基质的制备方法及应用 |
| CN120202411A (zh) * | 2022-11-18 | 2025-06-24 | 基因泰克公司 | 使用质量标签进行基于ia-lc-ms/ms的测定的信号放大和多重化 |
| WO2024238393A1 (fr) * | 2023-05-10 | 2024-11-21 | Northwestern University | Imagerie et spectrométrie de masse de caractérisation de protéoformes |
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| US4625014A (en) * | 1984-07-10 | 1986-11-25 | Dana-Farber Cancer Institute, Inc. | Cell-delivery agent |
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| KR100473903B1 (ko) | 1996-01-23 | 2005-09-30 | 퀴아진 지노믹스, 인코포레이티드 | 리간드쌍의결합을검출하는방법 |
| US5808300A (en) | 1996-05-10 | 1998-09-15 | Board Of Regents, The University Of Texas System | Method and apparatus for imaging biological samples with MALDI MS |
| CA2274587A1 (fr) * | 1996-12-10 | 1998-06-18 | Genetrace Systems Inc. | Molecules d'etiquetage massique, non volatiles et liberables |
| GB9815166D0 (en) * | 1998-07-13 | 1998-09-09 | Brax Genomics Ltd | Compounds for mass spectrometry |
| US20030215421A1 (en) | 1999-07-21 | 2003-11-20 | Mcdonald John R. | Methods and compositions for treating secondary tissue damage and other inflammatory conditions and disorders |
| CA2371843A1 (fr) | 1999-05-07 | 2000-11-16 | Yale University | Analyse a etiquetage multiple |
| US6824981B2 (en) | 2000-08-11 | 2004-11-30 | Agilix Corporation | Ultra-sensitive detection systems using alterable peptide tags |
| AU2002240423B2 (en) | 2001-02-14 | 2006-03-09 | Picoliter Inc. | Acoustic sample introduction for analysis and/or processing |
| US7183116B2 (en) * | 2001-05-14 | 2007-02-27 | The Institute For Systems Biology | Methods for isolation and labeling of sample molecules |
| US6756586B2 (en) * | 2001-10-15 | 2004-06-29 | Vanderbilt University | Methods and apparatus for analyzing biological samples by mass spectrometry |
| DE10238069A1 (de) * | 2002-08-19 | 2004-03-04 | N.V. Nutricia | MALDI-Matrix |
| GB0228429D0 (en) | 2002-12-05 | 2003-01-08 | Novartis Ag | Organic compounds |
| WO2005067648A2 (fr) | 2004-01-08 | 2005-07-28 | Vanderbilt University | Profilage spatial multiplex d'expression genique |
| US7588906B2 (en) | 2004-02-24 | 2009-09-15 | Wisconsin Alumni Research Foundation | Hydrogels for biomolecule analysis and corresponding method to analyze biomolecules |
| US7618780B2 (en) | 2004-05-20 | 2009-11-17 | Trillion Genomics Limited | Use of mass labelled probes to detect target nucleic acids using mass spectrometry |
-
2006
- 2006-06-07 AT AT06795327T patent/ATE528644T1/de not_active IP Right Cessation
- 2006-06-07 WO PCT/IB2006/002309 patent/WO2007000669A2/fr not_active Ceased
- 2006-06-07 AT AT06795326T patent/ATE520022T1/de not_active IP Right Cessation
- 2006-06-07 EP EP06795327A patent/EP1891426B1/fr not_active Not-in-force
- 2006-06-07 EP EP10167401.8A patent/EP2322921B1/fr not_active Not-in-force
- 2006-06-07 CA CA2611266A patent/CA2611266C/fr not_active Expired - Fee Related
- 2006-06-07 JP JP2008515318A patent/JP2008542784A/ja active Pending
- 2006-06-07 CA CA002611297A patent/CA2611297A1/fr not_active Abandoned
- 2006-06-07 US US11/916,558 patent/US8148676B2/en not_active Expired - Fee Related
- 2006-06-07 ES ES06795326T patent/ES2371203T3/es active Active
- 2006-06-07 EP EP10167400.0A patent/EP2322920B1/fr not_active Not-in-force
- 2006-06-07 EP EP06795326A patent/EP1889047B1/fr not_active Not-in-force
- 2006-06-07 EP EP10180422A patent/EP2287602A1/fr not_active Withdrawn
- 2006-06-07 EP EP10167398.6A patent/EP2325631B1/fr not_active Not-in-force
- 2006-06-07 WO PCT/IB2006/002311 patent/WO2007007192A1/fr not_active Ceased
- 2006-06-07 US US11/921,678 patent/US8221972B2/en not_active Expired - Fee Related
- 2006-06-07 JP JP2008515317A patent/JP5220593B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007007192A1 (fr) | 2007-01-18 |
| WO2007000669A3 (fr) | 2007-12-06 |
| ATE528644T1 (de) | 2011-10-15 |
| ATE520022T1 (de) | 2011-08-15 |
| JP2008542783A (ja) | 2008-11-27 |
| EP1889047B1 (fr) | 2011-08-10 |
| EP2325631B1 (fr) | 2015-01-28 |
| US20080203289A1 (en) | 2008-08-28 |
| EP2322921A1 (fr) | 2011-05-18 |
| WO2007000669A2 (fr) | 2007-01-04 |
| EP1891426B1 (fr) | 2011-10-12 |
| EP2322921B1 (fr) | 2014-08-06 |
| EP2322920B1 (fr) | 2014-12-10 |
| JP2008542784A (ja) | 2008-11-27 |
| EP1889047A2 (fr) | 2008-02-20 |
| ES2371203T3 (es) | 2011-12-28 |
| CA2611266C (fr) | 2015-11-24 |
| JP5220593B2 (ja) | 2013-06-26 |
| US8221972B2 (en) | 2012-07-17 |
| EP2325631A1 (fr) | 2011-05-25 |
| US20110151451A1 (en) | 2011-06-23 |
| US8148676B2 (en) | 2012-04-03 |
| EP2287602A1 (fr) | 2011-02-23 |
| CA2611297A1 (fr) | 2007-01-18 |
| EP2322920A1 (fr) | 2011-05-18 |
| WO2007007192A8 (fr) | 2008-04-17 |
| EP1891426A1 (fr) | 2008-02-27 |
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